Sodium Carbonate → (6-Chloro-2',6'-dimethylbiphenyl-3-yl)methanol

HRID 2426752Notes

Reaction equation

BrC1C=C(C=CC=1Cl)C(OC)=O.CC1C=CC=C(C)C=1B(O)O.[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+].[Cl:32][C:33]1[C:38]([C:39]2[C:44]([CH3:45])=[CH:43][CH:42]=[CH:41][C:40]=2[CH3:46])=[CH:37][C:36]([C:47](OC)=[O:48])=[CH:35][CH:34]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1.C(COC)OC.C(O)C.O>[Cl:32][C:33]1[C:38]([C:39]2[C:44]([CH3:45])=[CH:43][CH:42]=[CH:41][C:40]=2[CH3:46])=[CH:37][C:36]([CH2:47][OH:48])=[CH:35][CH:34]=1

Participants

Conditions

Temperature: 90 °C

Procedure

In an atmosphere of nitrogen, a mixture of methyl 3-bromo-4-chlorobenzoate, (2,6-dimethylphenyl)boronic acid, lithium chloride, sodium carbonate, water, ethanol, dimethoxyethane and tetrakis(triphenylphosphine)palladium was stirred at 90° C. for 15 hours, thereby obtaining methyl 6-chloro-2′,6′-dimethylbiphenyl-3-carboxylate. Lithium aluminum hydride was added under ice-cooling to a THF solution of the resulting methyl 6-chloro-2′,6′-dimethylbiphenyl-3-carboxylate, followed by warming up to room temperature and stirring for 2 hours to obtain (6-chloro-2′,6′-dimethylbiphenyl-3-yl)methanol.

Workup

temperatureby warming up to room temperature
stirringstirring for 2 hours

Sources & evidence

ORD record: ord-ecf86951a9094f1f853f9056dd7d8cc9
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968552B2

Reaction notes

Loading…